AT266128B - Process for the preparation of new oxazolidine derivatives - Google Patents
Process for the preparation of new oxazolidine derivativesInfo
- Publication number
- AT266128B AT266128B AT658866A AT658866A AT266128B AT 266128 B AT266128 B AT 266128B AT 658866 A AT658866 A AT 658866A AT 658866 A AT658866 A AT 658866A AT 266128 B AT266128 B AT 266128B
- Authority
- AT
- Austria
- Prior art keywords
- acid
- general formula
- ester
- radical
- compound
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A61K31/52—Purines, e.g. adenine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D263/06—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by oxygen atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- C07D263/24—Oxygen atoms attached in position 2 with hydrocarbon radicals, substituted by oxygen atoms, attached to other ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Herstellung von neuen Oxazolidinderivaten Gegenstand der Erfindung ist die Herstellung der neuen Verbindungen der allgemeinen Formel
EMI1.1
worin Z für ein Sauerstoff- oder Schwefelatom steht und R einen mindestens 2 und vorzugsweise nicht mehr als 4 Kohlenstoffatome aufweisenden niederen Alkenylrest bedeutet.
Der Rest R ist vorzugsweise der Vinylrest oder auch ein Propenyl-oder Butenylrest.
Die neuen Verbindungen besitzen wertvolle pharmakologische Eigenschaften. So hemmen sie insbesondere adrenergische ss-Rezeptoren, wie sich im Tierversuch, z. B. an Katzen und isolierten Meerschweinchenherzen, zeigt. Die neuen Verbindungen können daher bei Angina pectoris oder Herzrhythmusstörungen Verwendung finden. Die neuen Verbindungen sind ferner auch wertvolle Zwischenprodukte für die Herstellung von anderen nützlichen Stoffen, insbesondere von pharmakologisch wirksamen Verbindungen.
Besonders wertvoll bezüglich ihrer pharmakologischen Eigenschaften sind Verbindungen der allgemeinen Formel
EMI1.2
worin M für den Allyl- oder Methallylrest und Z für 0 oder S steht, und vor allem das 3-Isopropyl-5- (o-allyloxy-phenoxymethyl)-oxazolidinon- (2) der Formel
EMI1.3
das beispielsweise an Katzen bei intravenöser Gabe in Dosen von 0, 0 I bis 0, 1 mg/kg eine ausgesprochene ss-blockierende Wirkung aufweist.
<Desc/Clms Page number 2>
Die neuen Verbindungen werden nach an sich bekannten Methoden gewonnen.
Erfindungsgemäss geht man so vor, dass man einen Ester, ein Amid, ein Halogenid oder Anhydrid einer Säure der Formel
EMI2.1
worin Zi ein Sauerstoff- oder Schwefelatom bedeutet, R und Z die oben gegebenen Bedeutungen haben und Y eine freie Hydroxylgruppe oder, bei Verwendung des Carbaminsäureesters, auch eine reaktionsfähig veresterte Hydroxylgruppe bedeutet, intramolekular kondensiert.
Als Ester werden besonders Alkyl-, wie Methyl- oder Äthylester, oder Phenylester verwendet, Halogenide sind vor allem Chloride oder Bromide, Amide insbesondere Diphenylamide, Anhydride vor allem gemischte Anhydride, z. B. mit einer niederen Carbonsäure, wie besonders Essigsäure.
Eine reaktionsfähig veresterte Hydroxylgruppe ist besonders eine mit einer starken anorganischen oder organischen Säure, insbesondere einer Halogenwasserstoffsäure, wie Chlor-, Brom- oder Jodwasserstoff- säure, oder einer Sulfonsäure, vor allem einer Arylsulfonsäure, z. B. der p-Toluolsulfonsäure, veresterte Hydroxylgruppe.
Die Reaktion wird in üblicher Weise durchgeführt, vorzugsweise durch Erwärmen, in An-oder Abwesenheit von Lösungsmitteln, gegebenenfalls unter Zusatz von Kondensationsmitteln.
Die Ausgangsstoffe sind bekannt oder können nach an sich bekannten Methoden gewonnen werden.
Man kann ferner eine Verbindung der allgemeinen Formel
EMI2.2
mit einer Verbindung der Formel
EMI2.3
umsetzen, wobei R, Y, Zi und Z die oben gegebenen Bedeutungen haben und Y1 einen gegen die Isopropylaminogruppe austauschbaren Rest, wie vor allem eine veresterte oder verätherte Hydroxylgruppe darstellt, wodurch die entsprechende Verbindung (II) in situ gebildet und anschliessend zur entsprechenden Verbindung (I) intramolekular kondensiert wird.
Eine bevorzugte Ausführungsform des oben erwähnten Verfahrens ist die Umsetzung von 3- [o- (R- - CH2-O) -Phenoxy]-I-isopropylamino-propanol- (2), worin R die eben gegebene Bedeutung hat, mit einem Dihalogenid oder Diester der Kohlensäure oder Thiokohlensäure, vor allem mit Kohlensäurediäthylester oder Phosgen bzw. Thiophosgen.
Die neuen Verbindungen können als Racemate oder in Form der Antipoden vorliegen. Die Racemate lassen sich in üblicher Weise in die Antipoden zerlegen. Vorteilhaft isoliert man den wirksameren Antipoden.
Die neuen Verbindungen können z. B. in Form pharmazeutischer Präparate Verwendung finden, welche sie in Mischung mit einem für die enterale oder parenterale Applikation geeigneten pharmazeutischen organischen oder anorganischen, festen oder flüssigen Trägermaterial enthalten. Für die Bildung desselben kommen solche Stoffe in Frage, die mit den neuen Verbindungen nicht reagieren, wie z. B. Wasser, Gelatine, Lactose, Stärke, Stearylalkohol, Magnesiumstearat, Talk, pflanzliche Öle, Benzylalkohole, Gummi, Polyalkylenglykole, Vaseline oder andere bekannte Arzneimittelträger. Die pharmazeutischen Präparate können z. B. als Tabletten, Dragées, Kapseln oder in flüssiger Form als Lösungen, Suspensionen oder Emulsionen vorliegen.
Gegebenenfalls sind sie sterilisiert und/oder enthalten Hilfsstoffe, wie Konservierungs-, Stabilisierungs-, Netz-oder Emulgiermittel, Lösungsvermittler oder Salze zur Veränderung des osmotischen Druckes oder Puffer. Sie können auch andere therapeutisch wertvolle Substanzen, wie z. B. gefässerweiternde, insbesondere coronarerweiternde Verbindungen enthalten, wie vor allem gefässerweiternde
EMI2.4
<Desc/Clms Page number 3>
Die Erfindung wird in den folgenden Beispielen näher beschrieben. Die Temperaturen sind in Celsiusgraden angegeben.
Beispiel 1 : Zu 13, 0 g l-Isopropylamino-2-hydroxy-3- (o-allyloxyphenoxy)-propan in 150 m1 Toluol gibt man 5, 0 g fein gepulverte Pottasche und lässt unter Rühren bei Zimmertemperatur 30 ml einer Lösung von Phosgen in Toluol (20%ig) zutropfen. Nach 6 h filtriert man den ausgefallenen Niederschlag ab und dampft das Filtrat im Wasserstrahlvakuum ein. Es verbleibt ein Öl, das langsam kristallisiert. Durch Umkristallisation aus Methylenchlorid-Petroläther erhält man das 3-Isopropyl-5- (o-allyloxy-phenoxymethyl)- oxazolidinon- (2) der Formel
EMI3.1
in Kristallen vom F. 58-60 .
Das Ausgangsmaterial wird auf folgende Weise erhalten :
75 g Brenzkatechin-monoallyläther, 75 g Epichlorhydrin, 75 g Pottasche und 400 ml Aceton werden unter Rühren während 12 h zum Sieden erhitzt. Die Pottasche wird hierauf abfiltriert. Das Lösungsmittel destilliert man im Wasserstrahlvakuum ab. Es verbleibt ein Öl, das man in Äther löst und mit 2 n-Natronlauge ausschüttelt. Der Äther wird abgetrennt, getrocknet und abdestilliert. Den verbleibenden Rückstand destilliert man im Wasserstrahlvakuum. Das 3- (0-Allyloxy-phenoxy) -1, 2-epoxy-propan destilliert bei Kpl1 ; 145-157 o.
Eine Lösung von 15 g 3- (o-Allyloxy-phenoxy) -1, 2-epoxy-propan und 15 g Isopropylamin in 20 ml Äthanol wird während 4 h unter Rückfluss gekocht. Das überschüssige Amin und der Alkohol werden im Vakuum abdestilliert. Es verbleibt das l-Isopropylamino-2-hydroxy-3- (o-allyloxyphenoxy)-propan, das
EMI3.2
30 g Thiocarbonyl-bis-imidazol in 300 ml abs. Tetrahydrofuran wird während l h auf 80 0 erwärmt. Anschliessend wird das Lösungsmittel abdestilliert. Den Rückstand löst man in Äther. Man extrahiert mit 2 n-Salzsäure und 2 n-Natronlauge und engt die organische Phase im Vakuum ein. Der verbleibende Rückstand wird in Benzol gelöst und durch Aluminiumoxyd filtriert.
Nach dem Eindampfen des Benzols verbleibt das 3- Isopropyl-5- (o-allyloxy-phenoxymethyl) -oxazoliclinthion- (2) der Formel
EMI3.3
das nach Umkristallisation aus Methylenchlorid-Petroläther bei 92-940 schmilzt.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the preparation of new oxazolidine derivatives The invention relates to the preparation of the new compounds of the general formula
EMI1.1
where Z stands for an oxygen or sulfur atom and R stands for a lower alkenyl radical having at least 2 and preferably not more than 4 carbon atoms.
The radical R is preferably the vinyl radical or also a propenyl or butenyl radical.
The new compounds have valuable pharmacological properties. In particular, they inhibit adrenergic SS receptors, as shown in animal experiments, e.g. B. on cats and isolated guinea pig hearts shows. The new compounds can therefore be used in angina pectoris or cardiac arrhythmias. The new compounds are also valuable intermediates for the preparation of other useful substances, in particular pharmacologically active compounds.
Compounds of the general formula are particularly valuable with regard to their pharmacological properties
EMI1.2
wherein M stands for the allyl or methallyl radical and Z stands for 0 or S, and above all 3-isopropyl-5- (o-allyloxyphenoxymethyl) -oxazolidinone- (2) of the formula
EMI1.3
which, for example, has a pronounced SS-blocking effect on cats when given intravenously in doses of 0.0 I to 0.1 mg / kg.
<Desc / Clms Page number 2>
The new compounds are obtained by methods known per se.
According to the invention, the procedure is that an ester, an amide, a halide or anhydride of an acid of the formula
EMI2.1
where Zi denotes an oxygen or sulfur atom, R and Z have the meanings given above and Y denotes a free hydroxyl group or, if the carbamic acid ester is used, also denotes a reactive esterified hydroxyl group, intramolecularly condensed.
Particularly alkyl, such as methyl or ethyl esters, or phenyl esters are used as esters, halides are primarily chlorides or bromides, amides, particularly diphenylamides, anhydrides, particularly mixed anhydrides, e.g. B. with a lower carboxylic acid, such as especially acetic acid.
A reactive esterified hydroxyl group is particularly one with a strong inorganic or organic acid, in particular a hydrohalic acid such as chloric, bromic or hydroiodic acid, or a sulfonic acid, especially an aryl sulfonic acid, eg. B. p-toluenesulfonic acid, esterified hydroxyl group.
The reaction is carried out in the customary manner, preferably by heating, in the presence or absence of solvents, optionally with the addition of condensing agents.
The starting materials are known or can be obtained by methods known per se.
You can also use a compound of the general formula
EMI2.2
with a compound of the formula
EMI2.3
convert, where R, Y, Zi and Z have the meanings given above and Y1 represents a radical that can be exchanged for the isopropylamino group, such as an esterified or etherified hydroxyl group, whereby the corresponding compound (II) is formed in situ and then to the corresponding compound ( I) is condensed intramolecularly.
A preferred embodiment of the above-mentioned process is the reaction of 3- [o- (R- - CH2-O) -phenoxy] -I-isopropylamino-propanol- (2), in which R has the meaning just given, with a dihalide or Diesters of carbonic acid or thiocarbonic acid, especially with carbonic acid diethyl ester or phosgene or thiophosgene.
The new compounds can exist as racemates or in the form of the antipodes. The racemates can be broken down into the antipodes in the usual way. It is advantageous to isolate the more effective antipode.
The new connections can e.g. B. can be used in the form of pharmaceutical preparations which contain them as a mixture with a pharmaceutical, organic or inorganic, solid or liquid carrier material suitable for enteral or parenteral administration. For the formation of the same substances come into question that do not react with the new compounds, such as. B. water, gelatin, lactose, starch, stearyl alcohol, magnesium stearate, talc, vegetable oils, benzyl alcohols, gum, polyalkylene glycols, petrolatum or other known excipients. The pharmaceutical preparations can e.g. B. as tablets, dragees, capsules or in liquid form as solutions, suspensions or emulsions.
If necessary, they are sterilized and / or contain auxiliaries, such as preservatives, stabilizers, wetting agents or emulsifiers, solubilizers or salts for changing the osmotic pressure or buffers. You can also use other therapeutically valuable substances, such as. B. contain vasodilator, especially coronary dilation compounds, such as especially vasodilator
EMI2.4
<Desc / Clms Page number 3>
The invention is described in more detail in the following examples. The temperatures are given in degrees Celsius.
Example 1: To 13.0 g of l-isopropylamino-2-hydroxy-3- (o-allyloxyphenoxy) propane in 150 ml of toluene, 5.0 g of finely powdered potash is added and 30 ml of a solution of phosgene are left with stirring at room temperature add dropwise in toluene (20%). After 6 hours, the precipitate is filtered off and the filtrate is evaporated in a water-jet vacuum. An oil remains that slowly crystallizes. Recrystallization from methylene chloride-petroleum ether gives 3-isopropyl-5- (o-allyloxyphenoxymethyl) -oxazolidinone- (2) of the formula
EMI3.1
in crystals from F. 58-60.
The starting material is obtained in the following way:
75 g of pyrocatechol monoallyl ether, 75 g of epichlorohydrin, 75 g of potash and 400 ml of acetone are heated to the boil for 12 hours while stirring. The potash is then filtered off. The solvent is distilled off in a water jet vacuum. An oil remains, which is dissolved in ether and shaken out with 2N sodium hydroxide solution. The ether is separated off, dried and distilled off. The remaining residue is distilled in a water jet vacuum. The 3- (0-allyloxyphenoxy) -1, 2-epoxy-propane distilled at Kpl1; 145-157 o.
A solution of 15 g of 3- (o-allyloxyphenoxy) -1, 2-epoxy-propane and 15 g of isopropylamine in 20 ml of ethanol is refluxed for 4 h. The excess amine and the alcohol are distilled off in vacuo. What remains is the l-isopropylamino-2-hydroxy-3- (o-allyloxyphenoxy) propane, which
EMI3.2
30 g of thiocarbonyl-bis-imidazole in 300 ml of abs. Tetrahydrofuran is heated to 80 ° for 1 h. The solvent is then distilled off. The residue is dissolved in ether. It is extracted with 2N hydrochloric acid and 2N sodium hydroxide solution and the organic phase is concentrated in vacuo. The remaining residue is dissolved in benzene and filtered through aluminum oxide.
After evaporation of the benzene, the 3-isopropyl-5- (o-allyloxy-phenoxymethyl) -oxazoliclinthione- (2) of the formula remains
EMI3.3
which melts at 92-940 after recrystallization from methylene chloride petroleum ether.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH1432269A CH490405A (en) | 1965-07-09 | 1965-07-09 | Process for the preparation of new oxazolidine derivatives |
CH962965A CH484172A (en) | 1965-07-09 | 1965-07-09 | Process for the preparation of a new oxazolidinone |
CH1585465A CH500216A (en) | 1965-07-09 | 1965-11-17 | 3-Isopropyl 5-phenoxymethyloxazolidines |
CH1585565A CH512504A (en) | 1965-07-09 | 1965-11-17 | Process for the preparation of new oxazolidin-2-one compounds |
CH505966A CH507271A (en) | 1965-07-09 | 1966-04-06 | Oxazolidinones inhibiting adrenergic beta-receptors |
CH667066 | 1966-05-06 |
Publications (1)
Publication Number | Publication Date |
---|---|
AT266128B true AT266128B (en) | 1968-11-11 |
Family
ID=27543759
Family Applications (6)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AT587767A AT266129B (en) | 1965-07-09 | 1966-07-08 | Process for the preparation of oxazolidine derivatives and their salts |
AT587667A AT266832B (en) | 1965-07-09 | 1966-07-08 | Process for the preparation of new oxazolidine derivatives and their salts |
AT635867A AT268276B (en) | 1965-07-09 | 1966-07-08 | Process for the preparation of new oxazolidine derivatives |
AT636367A AT269137B (en) | 1965-07-09 | 1966-07-08 | Process for the preparation of new oxazolidine derivatives |
AT658866A AT266128B (en) | 1965-07-09 | 1966-07-08 | Process for the preparation of new oxazolidine derivatives |
AT658766A AT266127B (en) | 1965-07-09 | 1966-07-08 | Process for the preparation of new oxazolidine derivatives and their salts |
Family Applications Before (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AT587767A AT266129B (en) | 1965-07-09 | 1966-07-08 | Process for the preparation of oxazolidine derivatives and their salts |
AT587667A AT266832B (en) | 1965-07-09 | 1966-07-08 | Process for the preparation of new oxazolidine derivatives and their salts |
AT635867A AT268276B (en) | 1965-07-09 | 1966-07-08 | Process for the preparation of new oxazolidine derivatives |
AT636367A AT269137B (en) | 1965-07-09 | 1966-07-08 | Process for the preparation of new oxazolidine derivatives |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AT658766A AT266127B (en) | 1965-07-09 | 1966-07-08 | Process for the preparation of new oxazolidine derivatives and their salts |
Country Status (11)
Country | Link |
---|---|
US (2) | US3455946A (en) |
AT (6) | AT266129B (en) |
BE (2) | BE683867A (en) |
BR (2) | BR6681111D0 (en) |
CH (4) | CH484172A (en) |
DE (2) | DE1670357A1 (en) |
DK (2) | DK126116B (en) |
FR (4) | FR1503574A (en) |
GB (2) | GB1108538A (en) |
NL (2) | NL6609640A (en) |
SE (2) | SE324775B (en) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3546231A (en) * | 1968-05-03 | 1970-12-08 | Ansul Co | Certain 2-(pyridyl-3-thiocarbamoyl-1,3-oxazolidines) |
AR207554A1 (en) * | 1972-12-02 | 1976-10-15 | Otsuka Pharma Co Ltd | PROCEDURE TO PRODUCE DERIVATIVES OF 3-ALKYL-5 - ((3,4-DIHYDRO-5-CARBOSTIRIL) OXIMETHYL) -OXAZOLIDINONE- (2) |
IT1109002B (en) * | 1977-09-22 | 1985-12-16 | Menarini Sas | DERIVATIVES OF 2 OXAZOLIDONE AND THEIR PREPARATION METHODS |
DE3205457A1 (en) * | 1982-02-16 | 1983-08-25 | Merck Patent Gmbh, 6100 Darmstadt | OXAZOLIDIN-2-ONE |
US4461773A (en) * | 1982-09-15 | 1984-07-24 | E. I. Dupont De Nemours And Company | P-Oxooxazolidinylbenzene compounds as antibacterial agents |
ES523901A0 (en) * | 1983-07-06 | 1985-04-01 | Fabr Prod Quimicos Y Farmaceut | A PROCEDURE FOR THE PREPARATION OF 3-SULFONAMIDOPYRIDINE 2-SUBSTITUTED DERIVATIVES. |
JP2008303145A (en) * | 2005-09-22 | 2008-12-18 | Takeda Chem Ind Ltd | Cardiotonic comprising grk inhibitor |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB834968A (en) * | 1957-08-28 | 1960-05-18 | Robins Co Inc A H | 5-o-alkoxyphenoxymethyl-2-oxazolidones |
NL131194C (en) * | 1963-07-19 |
-
1965
- 1965-07-09 CH CH962965A patent/CH484172A/en not_active IP Right Cessation
- 1965-07-09 CH CH1432269A patent/CH490405A/en not_active IP Right Cessation
- 1965-11-17 CH CH1585565A patent/CH512504A/en not_active IP Right Cessation
-
1966
- 1966-04-06 CH CH505966A patent/CH507271A/en not_active IP Right Cessation
- 1966-06-01 US US554317A patent/US3455946A/en not_active Expired - Lifetime
- 1966-06-20 GB GB27462/66A patent/GB1108538A/en not_active Expired
- 1966-06-20 GB GB27463/66D patent/GB1106594A/en not_active Expired
- 1966-06-30 DE DE19661670357 patent/DE1670357A1/en active Pending
- 1966-06-30 DE DE19661670358 patent/DE1670358A1/en active Pending
- 1966-07-05 FR FR68139A patent/FR1503574A/en not_active Expired
- 1966-07-08 DK DK354166AA patent/DK126116B/en unknown
- 1966-07-08 AT AT587767A patent/AT266129B/en active
- 1966-07-08 DK DK354266AA patent/DK125893B/en unknown
- 1966-07-08 BE BE683867D patent/BE683867A/xx unknown
- 1966-07-08 AT AT587667A patent/AT266832B/en active
- 1966-07-08 NL NL6609640A patent/NL6609640A/xx unknown
- 1966-07-08 AT AT635867A patent/AT268276B/en active
- 1966-07-08 AT AT636367A patent/AT269137B/en active
- 1966-07-08 BR BR181111/66A patent/BR6681111D0/en unknown
- 1966-07-08 BE BE683868D patent/BE683868A/xx unknown
- 1966-07-08 NL NL6609639A patent/NL6609639A/xx unknown
- 1966-07-08 AT AT658866A patent/AT266128B/en active
- 1966-07-08 AT AT658766A patent/AT266127B/en active
- 1966-07-08 SE SE9370/66A patent/SE324775B/xx unknown
- 1966-07-08 BR BR181113/66A patent/BR6681113D0/en unknown
- 1966-07-08 SE SE9371/66A patent/SE324571B/xx unknown
- 1966-07-13 FR FR76127A patent/FR5728M/fr not_active Expired
- 1966-09-13 FR FR76126A patent/FR5727M/fr not_active Expired
- 1966-09-27 FR FR77723A patent/FR6015M/fr not_active Expired
-
1967
- 1967-04-05 US US628520A patent/US3480640A/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
BE683868A (en) | 1967-01-09 |
GB1108538A (en) | 1968-04-03 |
BR6681113D0 (en) | 1973-12-26 |
BE683867A (en) | 1967-01-09 |
DE1670358A1 (en) | 1970-10-29 |
NL6609639A (en) | 1967-01-10 |
US3455946A (en) | 1969-07-15 |
CH484172A (en) | 1970-01-15 |
NL6609640A (en) | 1967-01-10 |
FR6015M (en) | 1968-05-06 |
AT266127B (en) | 1968-11-11 |
AT266832B (en) | 1968-12-10 |
SE324775B (en) | 1970-06-15 |
DK125893B (en) | 1973-05-21 |
FR5727M (en) | 1968-01-22 |
CH490405A (en) | 1970-05-15 |
US3480640A (en) | 1969-11-25 |
CH512504A (en) | 1971-09-15 |
FR1503574A (en) | 1967-12-01 |
AT268276B (en) | 1969-02-10 |
AT266129B (en) | 1968-11-11 |
DK126116B (en) | 1973-06-12 |
AT269137B (en) | 1969-03-10 |
SE324571B (en) | 1970-06-08 |
CH507271A (en) | 1971-05-15 |
DE1670357A1 (en) | 1970-10-29 |
FR5728M (en) | 1968-01-22 |
BR6681111D0 (en) | 1973-12-26 |
GB1106594A (en) | 1968-03-20 |
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